US7956210B2 - Iridium-catalyzed production method for organosilicon compounds - Google Patents
Iridium-catalyzed production method for organosilicon compounds Download PDFInfo
- Publication number
- US7956210B2 US7956210B2 US12/528,899 US52889908A US7956210B2 US 7956210 B2 US7956210 B2 US 7956210B2 US 52889908 A US52889908 A US 52889908A US 7956210 B2 US7956210 B2 US 7956210B2
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- US
- United States
- Prior art keywords
- carbon atoms
- formula
- radicals
- hydrocarbon
- compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- 239000003054 catalyst Substances 0.000 claims abstract description 19
- 150000001875 compounds Chemical class 0.000 claims abstract description 12
- 229910052741 iridium Inorganic materials 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 6
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910000077 silane Inorganic materials 0.000 claims abstract description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 37
- 229930195733 hydrocarbon Natural products 0.000 claims description 37
- -1 bicyclic compound Chemical class 0.000 claims description 29
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 18
- 239000000460 chlorine Substances 0.000 claims description 17
- 229910052801 chlorine Inorganic materials 0.000 claims description 15
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 238000004821 distillation Methods 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 150000001923 cyclic compounds Chemical class 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 7
- 150000004756 silanes Chemical class 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 150000002504 iridium compounds Chemical class 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000004122 cyclic group Chemical group 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 abstract description 18
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 abstract description 7
- 150000001343 alkyl silanes Chemical class 0.000 abstract description 3
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 abstract description 2
- 150000004291 polyenes Chemical class 0.000 abstract 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 abstract 1
- 239000000047 product Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 10
- 0 *[Si]([1*])([3*])[H] Chemical compound *[Si]([1*])([3*])[H] 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 125000003342 alkenyl group Chemical group 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 150000005840 aryl radicals Chemical class 0.000 description 6
- 125000000753 cycloalkyl group Chemical group 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000010626 work up procedure Methods 0.000 description 6
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- YGHUUVGIRWMJGE-UHFFFAOYSA-N chlorodimethylsilane Chemical compound C[SiH](C)Cl YGHUUVGIRWMJGE-UHFFFAOYSA-N 0.000 description 3
- VYXHVRARDIDEHS-UHFFFAOYSA-N 1,5-cyclooctadiene Chemical compound C1CC=CCCC=C1 VYXHVRARDIDEHS-UHFFFAOYSA-N 0.000 description 2
- 239000004912 1,5-cyclooctadiene Substances 0.000 description 2
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 2
- BJLJNLUARMMMLW-UHFFFAOYSA-N chloro-(3-chloropropyl)-dimethylsilane Chemical compound C[Si](C)(Cl)CCCCl BJLJNLUARMMMLW-UHFFFAOYSA-N 0.000 description 2
- 229910000510 noble metal Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 101000623895 Bos taurus Mucin-15 Proteins 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 239000005062 Polybutadiene Substances 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000007767 bonding agent Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 238000010517 secondary reaction Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/12—Organo silicon halides
- C07F7/14—Preparation thereof from optionally substituted halogenated silanes and hydrocarbons hydrosilylation reactions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/46—Ruthenium, rhodium, osmium or iridium
Definitions
- the invention relates to a process for preparing substituted alkylsilanes by addition of silanes having an Si—H bond onto unsaturated aliphatics in the presence of a specific Ir catalyst/cocatalyst system.
- Substituted alkylsilanes are of tremendous economic interest for many fields. They are used, for example, as bonding agents or as crosslinkers.
- iridium catalysts are used in the hydrosilylation of allyl compounds by alkoxy-substituted silanes.
- the Japanese patent JP 07126271 A is concerned with the hydrosilylation of allyl halides by chlorodimethylsilane. Disadvantages of these processes are either moderate yields, an uneconomically high catalyst concentration and/or a very short catalyst life.
- DE 10053037 C and EP 1156052 A describe processes in which low molecular weight, preferably cyclic dienes are added as cocatalysts in order to reduce the amounts of catalyst required.
- these cocatalysts have the disadvantage that they also react with the corresponding silanes and these reaction products are difficult to separate off from the desired target products by distillation.
- reaction bottoms after conclusion of the reaction are contaminated with noble metal residues and a further isolation/concentration of the residues by extraction or precipitation cannot be carried out commercially, so that the reaction bottoms have to be worked up in their entirety.
- the invention provides a process for preparing silanes of the general formula I
- R 9a , R 9b , R 9c , R 9d are each hydrogen or a hydrocarbon radical which may be unsubstituted or substituted by F, Cl, OR, NR′ 2 , CN or NCO and having from 1 to 18 carbon atoms, where the carbon chain can be interrupted by nonadjacent —O— groups, where 2 or 3 radicals selected from among R 9a , R 9b , R 9c , R 9d can together form a cyclic compound,
- the catalyst system comprising the iridium compound of the general formula IV and polymeric cocatalysts having structural units of the general formulae VI-VIII has a long life, ensures high product yields and product purity at very small amounts of catalyst and allows the reaction to be carried out either continuously or batchwise. Noble metal residues can easily be removed from the reaction bottoms.
- the silanes of the general formula I are usually formed in yields of at least 95%.
- the crude products of the general formula I which are prepared in this way by the process of the invention are obtained in a purity of up to 98%, so that, depending on the field of use, a work-up by distillation may even be able to be dispensed with. After the products of the general formula I have been separated off by distillation, the distillation bottoms can be reused for a reaction without further work-up.
- the hydrocarbon radicals R 1 , R 2 , R 3 are preferably alkyl, alkenyl, cycloalkyl, aryl radicals or Cl.
- the hydrocarbon radicals R 1 , R 2 , R 3 preferably do not have any substituents.
- the hydrocarbon radicals R 1 , R 2 , R 3 preferably have from 1 to 6 carbon atoms.
- Particularly preferred radicals are methyl, ethyl, propyl and phenyl.
- Preferred alkoxy radicals have from 1 to 6 carbon atoms.
- Particularly preferred radicals are methyl, ethyl, propyl and Cl.
- the hydrocarbon radicals R 4 , R 5 , R 6 are preferably alkyl, alkenyl, cycloalkyl or aryl radicals.
- the substituents on the hydrocarbon radicals R 4 , R 5 , R 6 are preferably chlorine or bromine.
- the hydrocarbon radicals R 4 , R 5 , R 6 preferably have from 1 to 10 carbon atoms. Particularly preferred radicals are methyl, chloroethyl, propyl and phenyl.
- the cyclic compound formed by R 4 , R 5 , R 6 preferably has from 5 to 15 carbon atoms.
- the hydrocarbon radicals R 7 are preferably alkyl, alkenyl, cycloalkyl or aryl radicals.
- the hydrocarbon radicals R 7 preferably do not have any substituents.
- the hydrocarbon radicals R 7 preferably have from 1 to 10 carbon atoms. Particularly preferred radicals are methyl, ethyl, propyl and phenyl.
- the cyclic compound formed from 2 radicals R 7 preferably has from 5 to 15 carbon atoms.
- the hydrocarbon radicals R 8 are preferably alkyl, alkenyl, cycloalkyl or aryl radicals.
- the hydrocarbon radicals R 8 preferably do not have any substituents.
- the hydrocarbon radicals R 8 preferably have at least 2, in particular at least 5 carbon atoms, and preferably have not more than 200, in particular not more than 100 carbon atoms.
- the hydrocarbon radicals R 9a , R 9b , R 9c , R 9d are preferably alkyl, alkenyl, cycloalkyl or aryl radicals.
- the hydrocarbon radicals R 9a , R 9b , R 9c , R 9d preferably do not have any substituents.
- the hydrocarbon radicals R 9a , R 9b , R 9c , R 9d preferably have from 1 to 10 carbon atoms. Particularly preferred radicals are methyl, ethyl, propyl and phenyl.
- the cyclic compound formed from R 9a , R 9b , R 9c , R 9d preferably has from 5 to 15 carbon atoms.
- the hydrocarbon radicals R′ are preferably alkyl, alkenyl, cycloalkyl or aryl radicals.
- the hydrocarbon radicals R′ preferably do not have any substituents.
- the hydrocarbon radicals R′ preferably have from 1 to 6 carbon atoms. Particularly preferred radicals are methyl, ethyl, propyl and phenyl.
- l Preference is given to l, m being integers of at least 6, in particular at least 20 and not more than 2000, and in particular not more than 200.
- n being an integer of at least 10, in particular at least 50 and not more than 1000, and in particular not more than 200.
- the compound of the general formula II is preferably reacted in an excess of from 0.01 to 100 mol % of II, more preferably from 0.1 to 10 mol %, with an alkene of the general formula III.
- the iridium compound of the general formula IV is preferably used in a concentration of from 5 to 250 ppm, in particular from 10 to 50 ppm.
- the polymeric cocatalyst is preferably used in a concentration of from 50 to 50,000 ppm, in particular from 50 to 20,000 ppm.
- the “en” compound in the general formula IV preferably has two double bonds which are most preferably not conjugated. Particular preference is given to using a cyclic “en” compound. In a very particularly preferred case, [(cycloocta-1C,5C-diene)IrCl] 2 is used as catalyst.
- the polymeric cocatalyst can be conjugated or nonconjugated.
- Particularly preferred polymeric cocatalysts are polybutadienes having a molecular weight of from 200 to 200,000 g/mol, more preferably a molecular weight of from 500 to 20,000 g/mol and most preferably a molecular weight of from 1000 to 10,000 g/mol.
- Particular preference is likewise given to polymeric cocatalysts in which the proportion of structural units of the general formula VI (cis double bond) is at least 10% by weight, most preferably at least 20% by weight. Examples of such compounds are the Lithene® products from Synthomer, e.g. Lithene® N4-5000 polymer.
- reaction components of the general formula II together with the iridium catalyst of the general formula IV and, if desired, the polymeric cocatalyst are placed in a reaction vessel and the reaction components of the general formula III, if desired in admixture with the polymeric cocatalyst, are introduced while stirring.
- the reaction can, if appropriate, occur in solution in the target product of the general formula I.
- the target product of the general formula I together with catalyst and, if desired, polymeric cocatalyst are placed in a reaction vessel and a mixture of component II, III and, if desired, the polymeric cocatalyst is introduced.
- the reaction time to be employed is preferably from 0.1 to 2000 minutes.
- the reaction is preferably carried out at a temperature of from 0 to 300° C., in particular from 20° C. to 200° C.
- the use of superatmospheric pressure may also be useful, preferably up to 100 bar.
- distillation bottoms were no longer catalytically active and could not be used in a further reaction, but instead had to be worked up directly to recover iridium.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102007011158A DE102007011158A1 (de) | 2007-03-07 | 2007-03-07 | Iridiumkatalysiertes Herstellungsverfahren für siliciumorganische Verbindungen |
| DE102007011158.6 | 2007-03-07 | ||
| DE102007011158 | 2007-03-07 | ||
| PCT/EP2008/052237 WO2008107332A1 (de) | 2007-03-07 | 2008-02-25 | Iridiumkatalysiertes herstellungsverfahren für siliciumorganische verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| US20100022793A1 US20100022793A1 (en) | 2010-01-28 |
| US7956210B2 true US7956210B2 (en) | 2011-06-07 |
Family
ID=39310655
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US12/528,899 Expired - Fee Related US7956210B2 (en) | 2007-03-07 | 2008-02-25 | Iridium-catalyzed production method for organosilicon compounds |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7956210B2 (de) |
| EP (1) | EP2121709B1 (de) |
| JP (1) | JP5032595B2 (de) |
| KR (1) | KR101143103B1 (de) |
| CN (1) | CN101646681B (de) |
| AT (1) | ATE473988T1 (de) |
| DE (2) | DE102007011158A1 (de) |
| WO (1) | WO2008107332A1 (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10968317B2 (en) | 2017-06-26 | 2021-04-06 | Dow Silicones Corporation | Method for hydrosilylation of aliphatically unsaturated alkoxysilanes and hydrogen terminated organosiloxane oligomers to prepare alkoxysilyl terminated polymers useful for functionalizing polyorganosiloxanes using an iridium catalyst |
| US11028297B2 (en) | 2017-08-22 | 2021-06-08 | Dow Silicones Corporation | Dual cure adhesive composition and methods for its preparation and use |
Citations (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2823218A (en) | 1955-12-05 | 1958-02-11 | Dow Corning | Process for the production of organo-silicon compounds |
| US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
| US3296291A (en) | 1962-07-02 | 1967-01-03 | Gen Electric | Reaction of silanes with unsaturated olefinic compounds |
| US3564266A (en) | 1968-04-08 | 1971-02-16 | Gen Electric | Photoelectric fingerprint ridge counter |
| US4658050A (en) | 1986-03-31 | 1987-04-14 | Union Carbide Corporation | Novel process for the preparation of halopropyltrialkoxysilanes and halopropylalkylalkoxysilanes |
| JPH06100572A (ja) | 1992-07-31 | 1994-04-12 | Shin Etsu Chem Co Ltd | ハロプロピルアルコキシシラン類の製造方法 |
| JPH07126271A (ja) | 1993-10-28 | 1995-05-16 | Shin Etsu Chem Co Ltd | ハロプロピルジメチルクロロシランの製造方法およびその合成用の触媒 |
| EP0709392A1 (de) | 1994-10-25 | 1996-05-01 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von 3-Halogen- bzw. -Pseudohalogen-alkylsilanestern |
| US5616762A (en) | 1994-10-25 | 1997-04-01 | Huels Aktiengesellschaft | Process for the preparation of 3-halo-and pseudohalo-alkylsilane esters |
| EP1156052A2 (de) | 2000-05-15 | 2001-11-21 | Shin-Etsu Chemical Co., Ltd. | Verfahren zur Herstellung von Halopropyldimethylchlorosilanen |
| DE10053037C1 (de) | 2000-10-26 | 2002-01-17 | Consortium Elektrochem Ind | Herstellung von Organosilanen |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5310565B2 (de) * | 1972-02-21 | 1978-04-14 | ||
| DE2835943A1 (de) * | 1978-08-17 | 1980-03-20 | Heyl & Co | Polymere hydrierkatalysatoren, verfahren zur herstellung dieser katalysatoren und ihre verwendung fuer homogene hydrierungen |
| AU4854197A (en) * | 1996-12-24 | 1998-06-25 | Dow Corning Corporation | Filled addition curable compositions having reduced gassing and increased shelf stability |
| JP2001131231A (ja) * | 1999-11-09 | 2001-05-15 | Kanegafuchi Chem Ind Co Ltd | ヒドロシリル化を利用したシリル化物の製造方法及び該シリル化物 |
| JP2001262040A (ja) * | 2000-03-15 | 2001-09-26 | Kanegafuchi Chem Ind Co Ltd | プライマー組成物および接着方法 |
| US6458995B1 (en) * | 2000-03-31 | 2002-10-01 | Celanese International Corporation | Catalytic composition for carbonylation including iridium and pyridine polymers |
| DE10232663C1 (de) * | 2002-07-18 | 2003-10-16 | Wacker Chemie Gmbh | Kontinuierliche Herstellung von Organosilanen |
| FR2856402B1 (fr) * | 2003-06-17 | 2005-08-26 | Rhodia Chimie Sa | Procede de preparation d'halogenoalkylchlorosilane |
| US20090036702A1 (en) | 2004-10-28 | 2009-02-05 | Wacker Chemie Ag | Production of organosilanes in the presence of iridium-catalysts and cocatalysts |
| DE102004058000A1 (de) * | 2004-12-01 | 2006-06-08 | Wacker Chemie Ag | Verfahren zur kontinuierlichen Hydrosilylierung |
-
2007
- 2007-03-07 DE DE102007011158A patent/DE102007011158A1/de not_active Withdrawn
-
2008
- 2008-02-25 CN CN2008800072869A patent/CN101646681B/zh not_active Expired - Fee Related
- 2008-02-25 DE DE502008000948T patent/DE502008000948D1/de active Active
- 2008-02-25 US US12/528,899 patent/US7956210B2/en not_active Expired - Fee Related
- 2008-02-25 WO PCT/EP2008/052237 patent/WO2008107332A1/de active Application Filing
- 2008-02-25 AT AT08709202T patent/ATE473988T1/de active
- 2008-02-25 JP JP2009552164A patent/JP5032595B2/ja not_active Expired - Fee Related
- 2008-02-25 KR KR1020097019168A patent/KR101143103B1/ko not_active IP Right Cessation
- 2008-02-25 EP EP08709202A patent/EP2121709B1/de not_active Not-in-force
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2823218A (en) | 1955-12-05 | 1958-02-11 | Dow Corning | Process for the production of organo-silicon compounds |
| US3159601A (en) | 1962-07-02 | 1964-12-01 | Gen Electric | Platinum-olefin complex catalyzed addition of hydrogen- and alkenyl-substituted siloxanes |
| US3296291A (en) | 1962-07-02 | 1967-01-03 | Gen Electric | Reaction of silanes with unsaturated olefinic compounds |
| US3564266A (en) | 1968-04-08 | 1971-02-16 | Gen Electric | Photoelectric fingerprint ridge counter |
| US4658050A (en) | 1986-03-31 | 1987-04-14 | Union Carbide Corporation | Novel process for the preparation of halopropyltrialkoxysilanes and halopropylalkylalkoxysilanes |
| JPH06100572A (ja) | 1992-07-31 | 1994-04-12 | Shin Etsu Chem Co Ltd | ハロプロピルアルコキシシラン類の製造方法 |
| JPH07126271A (ja) | 1993-10-28 | 1995-05-16 | Shin Etsu Chem Co Ltd | ハロプロピルジメチルクロロシランの製造方法およびその合成用の触媒 |
| EP0709392A1 (de) | 1994-10-25 | 1996-05-01 | Hüls Aktiengesellschaft | Verfahren zur Herstellung von 3-Halogen- bzw. -Pseudohalogen-alkylsilanestern |
| US5616762A (en) | 1994-10-25 | 1997-04-01 | Huels Aktiengesellschaft | Process for the preparation of 3-halo-and pseudohalo-alkylsilane esters |
| EP1156052A2 (de) | 2000-05-15 | 2001-11-21 | Shin-Etsu Chemical Co., Ltd. | Verfahren zur Herstellung von Halopropyldimethylchlorosilanen |
| US6359161B2 (en) * | 2000-05-15 | 2002-03-19 | Shin-Etsu Chemical Co., Ltd. | Preparation of halopropyldimethylchlorosilanes |
| DE10053037C1 (de) | 2000-10-26 | 2002-01-17 | Consortium Elektrochem Ind | Herstellung von Organosilanen |
| US20020052520A1 (en) | 2000-10-26 | 2002-05-02 | Andreas Bauer | Preparation of organosilanes |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10968317B2 (en) | 2017-06-26 | 2021-04-06 | Dow Silicones Corporation | Method for hydrosilylation of aliphatically unsaturated alkoxysilanes and hydrogen terminated organosiloxane oligomers to prepare alkoxysilyl terminated polymers useful for functionalizing polyorganosiloxanes using an iridium catalyst |
| US11028297B2 (en) | 2017-08-22 | 2021-06-08 | Dow Silicones Corporation | Dual cure adhesive composition and methods for its preparation and use |
Also Published As
| Publication number | Publication date |
|---|---|
| DE102007011158A1 (de) | 2008-09-11 |
| ATE473988T1 (de) | 2010-07-15 |
| KR20090119907A (ko) | 2009-11-20 |
| EP2121709A1 (de) | 2009-11-25 |
| CN101646681B (zh) | 2012-07-11 |
| DE502008000948D1 (de) | 2010-08-26 |
| JP2010520249A (ja) | 2010-06-10 |
| WO2008107332A1 (de) | 2008-09-12 |
| EP2121709B1 (de) | 2010-07-14 |
| US20100022793A1 (en) | 2010-01-28 |
| CN101646681A (zh) | 2010-02-10 |
| KR101143103B1 (ko) | 2012-05-24 |
| JP5032595B2 (ja) | 2012-09-26 |
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